Chloromethyl chloroformate → HCID 58958555, Verbindung

HRID 915278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915278
[O:1]=[S:2]1(=[O:26])[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][CH2:3]1.CC(C)([O-])C.[Li+].Cl[C:34]([O:36][CH2:37][Cl:38])=[O:35]>C(Cl)Cl.CC#N.O>[Cl:38][CH2:37][O:36][C:34](=[O:35])[N:20]([C:21](=[O:23])[CH3:22])[CH2:19][C@@H:17]1[O:16][C:15](=[O:24])[N:14]([C:11]2[CH:12]=[CH:13][C:8]([CH:5]3[CH2:4][CH2:3][S:2](=[O:1])(=[O:26])[CH2:7][CH2:6]3)=[C:9]([F:25])[CH:10]=2)[CH2:18]1

Komponenten

7

Edukt 3

HCID 62754Chloromethyl chloroformateHCID 478257188974-61-0HCID 236647642-Propanol, 2-methyl-, lithium salt (1:1)

Produkt 1

HCID 58958555HCID 58958555, VerbindungAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

(S)-N-{3-[4-(1,1-Dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1) (2.0 g, 5.2 mmol) in 13 mL of CH2Cl2 and 13 mL of CH3CN is cooled to 0° C. Lithium t-butoxide (1.0 M in hexanes, 5.7 mL, 5.7 mmol) is added and the mixture is stirred at 0° C. for 25 min and then at RT for 10 min. The mixture is re-cooled to 0° C. and chloromethyl chloroformate (0.6 mL, 6.2 mmol) is added dropwise. The mixture is stirred for 10 min at 0° C. and then allowed to stir at RT overnight. The solution is diluted with CH2Cl2 and water and the layers are separated. The organic layer is washed with water, brine, dried over Na2SO4, and conc in vacuo. Purification by silica gel chromatography afforded the title compound in 74% yield (1.8 g). 1H NMR (400 MHz, CDCl3): δ 7.47 (dd, 1H), 7.22 (t, 1H), 7.13 (dd, 1H), 5.91 (d, 1H), 5.76 (d, 1H), 4.82 (m, 1H), 4.16 (m, 1H), 4.07 (m, 2H), 3.69 (dd, 1H), 3.10 (m, 5H), 2.58 (s, 3H), 2.38 (m, 2H), 2.17 (m, 2H). MS-APCI (m/z+): 341, 385, 477.

Aufarbeitung

  1. waitat RT for 10 min
  2. temperatureThe mixture is re-cooled to 0° C.
  3. stirringThe mixture is stirred for 10 min at 0° C.
  4. stirringto stir at RT overnight
  5. customthe layers are separated
  6. washThe organic layer is washed with water, brine
  7. dry with materialdried over Na2SO4
  8. customPurification by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5e9afc145d4b4a9d9e661f4bc33ddc49
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265140B2

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